Sponge-associated sp. RM66 metabolome induction with N-acetylglucosamine: Antibacterial, antifungal and anti-trypanosomal activities

Abdel-Mageed, 2010, Dermacozines, a new phenazine family from deep-sea dermacocci isolated from a Mariana Trench sediment, Org. Biomol. Chem., 8, 2352, 10.1039/c001445a Abdelfattah, 2011, Izumiphenazine D, a new phenazoquinoline N-oxide from Streptomyces sp. IFM 11204, Chem. Pharm. Bull. (Tokyo), 59, 508, 10.1248/cpb.59.508 Abdelmohsen, 2014, Diversity, abundance and natural products of marine sponge-associated actinomycetes, Nat. Prod. Rep., 31, 381, 10.1039/C3NP70111E Abdelmohsen, 2014, Dereplication strategies for targeted isolation of new antitrypanosomal actinosporins A and B from a marine sponge associated-Actinokineospora sp. EG49, Mar. Drugs, 12, 1220, 10.3390/md12031220 Abdelmohsen, 2015, Elicitation of secondary metabolism in actinomycetes, Biotechnol. Adv., 10.1016/j.biotechadv.2015.06.003 Abdelmohsen, 2012, Antioxidant and Anti-Protease Activities of Diazepinomicin from the Sponge-Associated Micromonospora Strain RV115, Mar. Drugs, 10, 2208, 10.3390/md10102208 Altschul, 1990, Basic local alignment search tool, J. Mol. Biol., 215, 403, 10.1016/S0022-2836(05)80360-2 Barnhart, 2006, Curli biogenesis and function, Annu. Rev. Microbiol., 60, 131, 10.1146/annurev.micro.60.080805.142106 Blunt, 2013, Marine natural products, Nat. Prod. Rep., 30, 237, 10.1039/C2NP20112G Bode, 2002, Big effects from small changes: possible ways to explore nature's chemical diversity, ChemBioChem, 3, 619, 10.1002/1439-7633(20020703)3:7<619::AID-CBIC619>3.0.CO;2-9 Brakhage, 2013, Regulation of fungal secondary metabolism, Nat. Rev. Microbiol., 11, 21, 10.1038/nrmicro2916 Bull, 2007, Marine actinobacteria: new opportunities for natural product search and discovery, Trends Microbiol., 15, 491, 10.1016/j.tim.2007.10.004 Chatterjee, 1995, Phencomycin, a new antibiotic from a Streptomyces species HIL Y-9031725, J. Antibiot. (Tokyo), 48, 1353, 10.7164/antibiotics.48.1353 Cheng, 2015, Biodiversity, anti-trypanosomal activity screening, and metabolomics profiling of actinomycetes isolated from Mediterranean sponges, PlOS ONE Chianese, 2012, Manadoperoxides, a new class of potent antitrypanosomal agents of marine origin, Org. Biomol. Chem., 10, 7197, 10.1039/c2ob26124c Cimermancic, 2014, Insights into Secondary Metabolism from a Global Analysis of Prokaryotic Biosynthetic Gene Clusters, Cell, 158, 412, 10.1016/j.cell.2014.06.034 Dashti, 2014, Production of induced secondary metabolites by a co-culture of sponge-associated actinomycetes, Actinokineospora sp. EG49 and Nocardiopsis sp. RV163, Mar. Drugs, 12, 3046, 10.3390/md12053046 Du, 2015, Regulation of gene expression in Pseudomonas aeruginosa M18 by phenazine-1-carboxylic acid, Appl. Microbiol. Biotechnol., 99, 813, 10.1007/s00253-014-6101-0 Eltamany, 2014, New antibacterial xanthone from the marine sponge-derived Micrococcus sp. EG45, Bioorg. Med. Chem. Lett., 24, 4939, 10.1016/j.bmcl.2014.09.040 Forner, 2013, Chemical dereplication of marine actinomycetes by liquid chromatography-high resolution mass spectrometry profiling and statistical analysis, Anal. Chim. Acta, 805, 70, 10.1016/j.aca.2013.10.029 Frank, 2008, Clustering millions of tandem mass spectra, J Proteome Res., 7, 113, 10.1021/pr070361e Gong, 2009, Enhanced Production of Surfactin by Bacillus subtilis E8 Mutant Obtained by Ion Beam Implantation, Food Technol. Biotechnol., 47, 27 Grkovic, 2014, Two new antioxidant actinosporin analogues from the calcium alginate beads culture of sponge-associated Actinokineospora sp. strain EG49, Bioorg. Med. Chem. Lett., 24, 5089, 10.1016/j.bmcl.2014.08.068 Han, 2014, Structural elucidation and antimicrobial activity of new phencomycin derivatives isolated from Burkholderia glumae strain 411gr-6, J. Antibiot. (Tokyo), 67, 721, 10.1038/ja.2014.50 Harrison, 1998, Cyclic polyketide peroxides and acyclic diol analogues from the sponge Plakortis lita, J. Nat. Prod., 61, 1033, 10.1021/np980093m Harvey, 2015, The re-emergence of natural products for drug discovery in the genomics era, Nat. Rev. Drug Discov., 14, 111, 10.1038/nrd4510 Hou, 2012, Microbial strain prioritization using metabolomics tools for the discovery of natural products, Anal. Chem., 84, 4277, 10.1021/ac202623g Kameda, 1974, Antitumor activity of bacillus natto. V. Isolation and characterization of surfactin in the culture medium of Bacillus natto KMD 2311, Chem. Pharm. Bull., 22, 938, 10.1248/cpb.22.938 Katz, 1977, The peptide antibiotics of Bacillus: chemistry, biogenesis, and possible functions, Bacteriological Reviews, 41, 449, 10.1128/BR.41.2.449-474.1977 Kennedy, 2015, Phenazine-1-carboxamide (PCN) from Pseudomonas sp. strain PUP6 selectively induced apoptosis in lung (A549) and breast (MDA MB-231) cancer cells by inhibition of antiapoptotic Bcl-2 family proteins, Apoptosis, 20, 858, 10.1007/s10495-015-1118-0 Kim, 2006, Surfactin C inhibits platelet aggregation, J. Pharm. Pharmacol., 58, 867, 10.1211/jpp.58.6.0018 Konopka, 2012, N-acetylglucosamine functions in cell signaling, Scientifica, 2012, 15, 10.6064/2012/489208 Korgaonkar, 2011, Pseudomonas aeruginosa enhances production of an antimicrobial in response to N-acetylglucosamine and peptidoglycan, J. Bacteriol., 193, 909, 10.1128/JB.01175-10 Kracht, 1999, Antiviral and hemolytic activities of surfactin isoforms and their methyl ester derivatives, J. Antibiot., 52, 613, 10.7164/antibiotics.52.613 Krug, 2014, Secondary metabolomics: the impact of mass spectrometry-based approaches on the discovery and characterization of microbial natural products, Nat. Prod. Rep., 31, 768, 10.1039/c3np70127a Lee, 2003, Isolation and in vitro and in vivo activity against Phytophthora capsici and Colletotrichum orbiculare of phenazine-1-carboxylic acid from Pseudomonas aeruginosa strain GC-B26, Pest Manag. Sci., 59, 872, 10.1002/ps.688 Letzel, 2013, A genomic approach to the cryptic secondary metabolome of the anaerobic world, Nat. Prod. Rep., 30, 392, 10.1039/C2NP20103H Liu, 2013, Molecular Regulation of Antibiotic Biosynthesis in Streptomyces, Microbiol. Mol. Biol. Rev., 77, 112, 10.1128/MMBR.00054-12 Lum, 2015, Activity of novel synthetic peptides against Candida albicans, Sci. Rep., 5, 9657, 10.1038/srep09657 Luo, 2013, Activation and characterization of a cryptic polycyclic tetramate macrolactam biosynthetic gene cluster, Nat. Commun., 4, 2894, 10.1038/ncomms3894 Marmann, 2014, Co-Cultivation-A Powerful Emerging Tool for Enhancing the Chemical Diversity of Microorganisms, Mar. Drugs, 12, 1043, 10.3390/md12021043 Mayer, 2005, Comp. Biochem. Physiol. C Toxicol. Pharmacol., 140, 265, 10.1016/j.cca.2005.04.004 Moussian, 2008, The role of GlcNAc in formation and function of extracellular matrices, Comp. Biochem. Physiol. B: Biochem. Mol. Biol., 149, 215, 10.1016/j.cbpb.2007.10.009 Muller, 2014, Future potential for anti-infectives from bacteria - How to exploit biodiversity and genomic potential, Int. J. Med. Microbiol., 304, 3, 10.1016/j.ijmm.2013.09.004 Naseem, 2012, Novel roles for GlcNAc in cell signaling, Commun. Integr. Biol., 5, 156, 10.4161/cib.19034 Otoguro, 2010, In vitro and in vivo anti-Trypanosoma brucei activities of phenazinomycin and related compounds, J. Antibiot. (Tokyo), 63, 579, 10.1038/ja.2010.72 Pérez-Campo, 2001, Factors affecting the morphogenetic switch in Yarrowia lipolytica, Curr. Microbiol., 43, 429, 10.1007/s002840010333 Pettit, 2009, Mixed fermentation for natural product drug discovery, Appl. Microbiol. Biotechnol., 83, 19, 10.1007/s00253-009-1916-9 Pimentel-Elardo, 2010, Anti-parasitic compounds from Streptomyces sp. strains isolated from Mediterranean sponges, Mar. Drugs, 8, 373, 10.3390/md8020373 Pruesse, 2012, SINA: accurate high-throughput multiple sequence alignment of ribosomal RNA genes, Bioinformatics, 28, 1823, 10.1093/bioinformatics/bts252 Pusecker, 1997, Dihydrophencomycin methyl ester, a new phenazine derivative from a marine Streptomycete, J. Antibiot. (Tokyo), 50, 479, 10.7164/antibiotics.50.479 Raaijmakers, 1997, Frequency of Antibiotic-Producing Pseudomonas spp. in Natural Environments, Appl. Environ. Microbiol., 63, 881, 10.1128/AEM.63.3.881-887.1997 Rainville, 2014, Advances in liquid chromatography coupled to mass spectrometry for metabolic phenotyping, Trac-Trends Anal. Chem., 61, 181, 10.1016/j.trac.2014.06.005 Rigali, 2008, Feast or famine: the global regulator DasR links nutrient stress to antibiotic production by Streptomyces, EMBO Rep., 9, 670, 10.1038/embor.2008.83 Rubert, 2015, Advances in high-resolution mass spectrometry based on metabolomics studies for food - a review, Food Addit. Part a-Chem. Anal. Control Exposure Risk Assess., 32, 1685 Sarmin, 2013, Streptomyces kebangsaanensis sp. nov., an endophytic actinomycete isolated from an ethnomedicinal plant, which produces phenazine-1-carboxylic acid, Int. J. Syst. Evol. Microbiol., 63, 3733, 10.1099/ijs.0.047878-0 Simonetti, 1974, Yeast-mycelial conversion induced by N-acetyl-D-glucosamine in Candida albicans, Nature, 250, 344, 10.1038/250344a0 Sohanpal, 2004, Integrated regulatory responses of fimB to N-acetylneuraminic (sialic) acid and GlcNAc in Escherichia coli K-12, PNAS, 101, 16322, 10.1073/pnas.0405821101 Tawfike, 2019, New bioactive metabolites from the elicited marine sponge-derived bacterium Actinokineospora spheciospongiae sp. nov, AMB Expr., 9, 12, 10.1186/s13568-018-0730-0 Tawfike, 2013, Metabolomics and dereplication strategies in natural products, Methods Mol. Biol., 1055, 227, 10.1007/978-1-62703-577-4_17 Thomashow, 1990, Production of the antibiotic phenazine-1-carboxylic Acid by fluorescent pseudomonas species in the rhizosphere of wheat, Appl. Environ. Microbiol., 56, 908, 10.1128/AEM.56.4.908-912.1990 Tsukamoto, 1998, Acanthosterol sulfates A-J: ten new antifungal steroidal sulfates from a marine sponge Acanthodendrilla sp, J. Nat. Prod., 61, 1374, 10.1021/np980178n Vicente, 2013, Biodiversity of actinomycetes associated with Caribbean sponges and their potential for natural product discovery, Mar. Biotechnol. (NY), 15, 413, 10.1007/s10126-013-9493-4 Wei, 2010, OSMAC (one strain many compounds) approach in the research of microbial metabolites–a review, Wei Sheng Wu Xue Bao, 50, 701 Xu, 2015, Effects of phenazine-1-carboxylic acid on the biology of the plant-pathogenic bacterium Xanthomonas oryzae pv. oryzae, Pestic. Biochem. Physiol., 117, 39, 10.1016/j.pestbp.2014.10.006 Yang, 2013, Molecular Networking as a Dereplication Strategy, J. Nat. Prod., 76, 1686, 10.1021/np400413s Yuliana, 2011, Metabolomics for bioactivity assessment of natural products, Phytother. Res., 25, 157, 10.1002/ptr.3258 Zhao, 2011, Actinopolysporins A-C and tubercidin as a Pdcd4 stabilizer from the halophilic actinomycete Actinopolyspora erythraea YIM 90600, J. Nat. Prod., 74, 1990, 10.1021/np200603g Zhou, 2016, Biotechnological potential of a rhizosphere Pseudomonas aeruginosa strain producing phenazine-1-carboxylic acid and phenazine-1-carboxamide, World J. Microbiol. Biotechnol., 32, 50, 10.1007/s11274-015-1987-y Zhu, 2014, Triggers and cues that activate antibiotic production by actinomycetes, J. Ind. Microbiol. Biotechnol., 41, 371, 10.1007/s10295-013-1309-z Ziemert, 2014, Diversity and evolution of secondary metabolism in the marine actinomycete genus Salinispora, Proc. Natl. Acad. Sci. U S A, 111, E1130, 10.1073/pnas.1324161111 Zou, 2010, Interaction between the natural lipopeptide [Glu1, Asp5)] surfactin-C15 and hemoglobin in aqueous solution, Biomacromolecules, 11, 593, 10.1021/bm9011453